CA2494920A1 - Composes photochromes et electrochromes et methodes de synthese et d'utilisation correspondantes - Google Patents

Composes photochromes et electrochromes et methodes de synthese et d'utilisation correspondantes Download PDF

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Publication number: CA2494920A1
Authority: CA; Canada
Prior art keywords: compound; ring; isomer; polymer; solution
Prior art date: 2002-08-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

CA002494920A

Other languages

English (en)

Other versions

CA2494920C (fr

Inventor

Neil R. Branda

Andrea Peters

Anthony J. Wigglesworth

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Solutia Canada Inc

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-08-09

Filing date

2003-08-11

Publication date

2004-02-19

2003-08-11 Application filed by Individual filed Critical Individual

2004-02-19 Publication of CA2494920A1 publication Critical patent/CA2494920A1/fr

2013-01-22 Application granted granted Critical

2013-01-22 Publication of CA2494920C publication Critical patent/CA2494920C/fr

2023-08-11 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

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AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000004973 liquid crystal related substance Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000003446 memory effect Effects 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
ILBBNDNPTFGRJD-UHFFFAOYSA-N pent-1-ene Chemical compound C=CCCC.C=CCCC.C=CCCC.C=CCCC ILBBNDNPTFGRJD-UHFFFAOYSA-N 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
230000002688 persistence Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
238000001782 photodegradation Methods 0.000 description 1
238000007699 photoisomerization reaction Methods 0.000 description 1
150000004291 polyenes Chemical class 0.000 description 1
229920000123 polythiophene Polymers 0.000 description 1
YWAKXRMUMFPDSH-UHFFFAOYSA-N propyl ethylene Natural products CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000004832 voltammetry Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
- C09K2323/031—Polarizer or dye
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
- G03H1/02—Details of features involved during the holographic process; Replication of holograms without interference recording
- G03H2001/026—Recording materials or recording processes
- G03H2001/0264—Organic recording material
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H2260/00—Recording materials or recording processes
- G03H2260/50—Reactivity or recording processes
- G03H2260/52—Photochromic reactivity wherein light induces a reversible transformation between two states having different absorption spectra

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Plural Heterocyclic Compounds (AREA)
Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)

CA2494920A 2002-08-09 2003-08-11 Composes photochromes et electrochromes et methodes de synthese et d'utilisation correspondantes Expired - Lifetime CA2494920C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US40208102P	2002-08-09	2002-08-09
US60/402,081		2002-08-09
US44206303P	2003-01-24	2003-01-24
US60/442,063		2003-01-24
PCT/CA2003/001216 WO2004015024A1 (fr)	2002-08-09	2003-08-11	Composes photochromes et electrochromes et methodes de synthese et d'utilisation correspondantes

Publications (2)

Publication Number	Publication Date
CA2494920A1 true CA2494920A1 (fr)	2004-02-19
CA2494920C CA2494920C (fr)	2013-01-22

Family

ID=31720571

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2494920A Expired - Lifetime CA2494920C (fr)	2002-08-09	2003-08-11	Composes photochromes et electrochromes et methodes de synthese et d'utilisation correspondantes

Country Status (5)

Country	Link
US (2)	US7777055B2 (fr)
JP (1)	JP4410108B2 (fr)
AU (1)	AU2003257320A1 (fr)
CA (1)	CA2494920C (fr)
WO (1)	WO2004015024A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT505116B1 (de) *	2007-03-22	2012-04-15	At & S Ag	Tintenzusammensetzungen und deren verwendung
WO2013044371A1 (fr) *	2011-09-30	2013-04-04	Switch Materials, Inc.	Dérivés de diarylcyclopentène photochromes et électrochromes comme filtres optiques
WO2013106921A1 (fr) *	2012-01-20	2013-07-25	Switch Materials , Inc.	Filtre optique composite

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4742181B2 (ja) *	2004-03-09	2011-08-10	福岡県	新規フォトクロミック化合物
WO2005090654A1 (fr) *	2004-03-16	2005-09-29	University Of Delaware	Fibres, textiles et membranes photochromiques actives et adaptatives
WO2006125317A1 (fr) *	2005-05-25	2006-11-30	Switch Materials Inc.	Composes electrochromiques et photochromiques et synthese et utilisation de ceux-ci
US8329896B2 (en)	2007-12-20	2012-12-11	Nec Corporation	Spirooxazine radical derivatives and reversible isomerization reaction
US8687258B2 (en)	2009-06-11	2014-04-01	Switch Materials, Inc.	Variable transmittance optical filter and uses thereof
WO2010142019A1 (fr)	2009-06-11	2010-12-16	Switch Materials, Inc.	Filtre optique à transmittance variable et utilisations correspondantes
EP2652546A4 (fr)	2010-12-15	2014-09-10	Switch Materials Inc	Dispositifs optiques à transmittance variable
WO2012079160A1 (fr) *	2010-12-15	2012-06-21	Switch Materials, Inc.	Filtre optique à facteur de transmission variable avec système d'électrodes sensiblement coplanaires
WO2013123592A1 (fr) *	2012-02-23	2013-08-29	Switch Materials Inc.	Filtre optique à source de lumière
US9594285B2 (en)	2012-04-18	2017-03-14	Switch Materials, Inc.	System and method for controlling an optical filter assembly
JP6463673B2 (ja)	2012-05-29	2019-02-06	スイッチマテリアルズインコーポレイテッドＳｗｉｔｃｈＭａｔｅｒｉａｌｓＩｎｃ．	可変透過率層を含む光学フィルタ
US9810963B2 (en)	2013-03-07	2017-11-07	Switch Materials, Inc.	Seal and seal system for a layered device
EP3084519A4 (fr)	2013-12-19	2017-08-16	Switch Materials, Inc.	Objets commutables et procédés de fabrication
WO2016077918A1 (fr) *	2014-11-17	2016-05-26	Switch Materials Inc.	Compositions photochromes-électrochromes
EP3360008B1 (fr) *	2015-10-07	2024-12-04	Vitro Flat Glass LLC	Procédé de fabrication d'un panneau électrochromique
US11489483B2 (en)	2015-12-09	2022-11-01	Brian Patrick Janowski	Solar window construction and methods
CN107011317B (zh) *	2016-05-24	2020-03-20	北京大学	光致异构化合物及包含其的器件
WO2018033620A1 (fr)	2016-08-18	2018-02-22	Basf Se	Composition notamment pour l'impression ou le revêtement comprenant des polymères de polyuréthane
EP3284800A1 (fr)	2016-08-18	2018-02-21	Basf Se	Composition pour préparer une couche électrochrome
EP3284799A1 (fr)	2016-08-18	2018-02-21	Basf Se	Composition, particulièrement d'impression ou de revêtement comprenant des polymères (méth)acrylate
WO2018033621A1 (fr)	2016-08-18	2018-02-22	Basf Se	Composition pour la préparation d'une couche électrochromique
EP3284764A1 (fr)	2016-08-18	2018-02-21	Basf Se	Composition, particulièrement d'impression ou de revêtement comprenant des polymères de polyuréthane
US11333810B2 (en)	2017-08-25	2022-05-17	Solutia Canada Inc.	System of networked controllers, and method of operating a system of networked controllers
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JP6997812B2 (ja) *	2020-01-06	2022-02-10	ヴィトロフラットグラスリミテッドライアビリティカンパニー	エレクトロクロミックデバイス及びエレクトロクロミックデバイスを製造する方法
CN116157710A (zh)	2020-07-15	2023-05-23	首诺加拿大公司	用于车辆的动态镜
JP7598585B2 (ja) *	2020-09-01	2024-12-12	山田化学工業株式会社	ジアリールエテン化合物
CN114690534B (zh) *	2022-04-11	2025-03-07	西湖大学	掩模版、光刻装置、掩模版的制造方法和基于掩模版的光刻方法
CN119899382B (zh) *	2025-01-20	2025-11-21	烟台大学	一种二芳基乙烯聚合物及制备方法和应用

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0541265Y2 (fr)	1987-07-31	1993-10-19
GB8916860D0 (en)	1989-07-24	1989-09-06	Traqson Ltd	Novel photoactive compounds
DE4007636A1 (de)	1990-03-10	1991-09-12	Basf Ag	Photochrome monomere und hieraus hergestellte photochrome polymerisate
JPH03264573A (ja)	1990-03-13	1991-11-25	Kanebo Ltd	フルギド類の製造法
JP3051529B2 (ja)	1991-10-23	2000-06-12	株式会社巴川製紙所	ホトクロミック高分子材料
AU691645B2 (en)	1992-04-03	1998-05-21	California Institute Of Technology	High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof
US5312940A (en)	1992-04-03	1994-05-17	California Institute Of Technology	Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
JPH06240242A (ja)	1993-02-15	1994-08-30	Nippon Telegr & Teleph Corp <Ntt>	重合体フォトクロミック組成物
JP3264573B2 (ja)	1994-01-14	2002-03-11	株式会社三協精機製作所	小型モータ
JP3395854B2 (ja)	1994-02-02	2003-04-14	日立化成工業株式会社	酸化銅の化学還元液およびこれを用いた多層プリント配線板の製造方法
JPH07311979A (ja)	1994-03-24	1995-11-28	Sanyo Electric Co Ltd	光記録媒体及びその再生方法
JP3132630B2 (ja)	1994-08-25	2001-02-05	科学技術振興事業団	チオフェン誘導体の重合体とその製造法
JP3491704B2 (ja)	1994-10-21	2004-01-26	入江　　正浩	ジチエニルエテン系化合物及び該化合物からなるフォトクロミック材料
US5500033A (en)	1995-01-23	1996-03-19	The Boc Group, Inc.	Melt heating method
JPH10152679A (ja)	1996-11-22	1998-06-09	Mita Ind Co Ltd	光メモリ素子と、それを用いた電子写真感光体、エレクトロルミネッセンス素子、液晶表示素子、および空間光変調素子
FR2772266B1 (fr)	1997-12-12	2000-02-04	Oreal	Utilisation d'agent de coloration photochrome dans une composition cosmetique, et composition cosmetique le comprenant
EP0933375A1 (fr)	1997-12-17	1999-08-04	Amersham Life Science Ltd	Composés photochromiques
FR2774998A1 (fr)	1998-02-19	1999-08-20	Ecole Polytech	Materiau photochromique a variation stable d'indice de refraction et/ou de birefringence
JPH11256147A (ja)	1998-03-13	1999-09-21	Dainippon Printing Co Ltd	コレステリック液晶性フォトクロミック高分子材料及びそれを用いた光機能性媒体
US6479604B1 (en)	1998-08-17	2002-11-12	Korea Research Institute Of Chemical Technology	Diarylethene compound, photochromic diarylethene type copolymer and method for the production of the same
US6884553B2 (en)	1999-03-11	2005-04-26	Mitsubishi Chemical Corporation	Near-field optical recording medium and near-field optical recording method
US6359150B1 (en)	1999-08-31	2002-03-19	Kyocera Corporation	Photochromic compound and optical function device using the same
JP5271472B2 (ja)	2000-07-14	2013-08-21	スイッチマテリアルズインコーポレイテッド	新規なフォトクロミックポリマーおよびそれを調製する方法
FR2813697A1 (fr)	2000-09-04	2002-03-08	Dixet	Support securise de donnees a lecture optique
JP4025920B2 (ja)	2001-03-05	2007-12-26	入江　　正浩	フォトクロミック材料
KR100424862B1 (ko)	2001-03-06	2004-03-31	한국화학연구원	이속사졸기로 치환된 신규한 광변색성 디아릴에텐계 화합물
JP3870703B2 (ja)	2001-03-14	2007-01-24	ダイソー株式会社	新規ホトクロミック化合物、およびその製造法と用途
DE60238405D1 (de)	2001-06-15	2011-01-05	Masahiro Irie	Photochromes material und darauf basierender farbdosimeter
KR100501829B1 (ko)	2001-07-30	2005-07-20	한국화학연구원	디아릴에텐 유도체와 이를 이용한 광변색 박막
KR100482654B1 (ko)	2001-09-18	2005-04-13	한국화학연구원	광변색 나노 캡슐 및 그의 제조방법
KR20030025622A (ko)	2001-09-21	2003-03-29	한국화학연구원	비닐기 함유 디아릴에텐 단량체 및 이를 이용하여 제조한광활성 고분자
KR20030085251A (ko)	2002-04-29	2003-11-05	한국화학연구원	광변색 형광 중합체와 그 제조방법
WO2006125317A1 (fr)	2005-05-25	2006-11-30	Switch Materials Inc.	Composes electrochromiques et photochromiques et synthese et utilisation de ceux-ci

2003
- 2003-08-11 AU AU2003257320A patent/AU2003257320A1/en not_active Abandoned
- 2003-08-11 US US10/523,965 patent/US7777055B2/en active Active
- 2003-08-11 JP JP2004526557A patent/JP4410108B2/ja not_active Expired - Lifetime
- 2003-08-11 CA CA2494920A patent/CA2494920C/fr not_active Expired - Lifetime
- 2003-08-11 WO PCT/CA2003/001216 patent/WO2004015024A1/fr not_active Ceased
2010
- 2010-07-01 US US12/828,756 patent/US8450503B2/en not_active Expired - Fee Related

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT505116B1 (de) *	2007-03-22	2012-04-15	At & S Ag	Tintenzusammensetzungen und deren verwendung
WO2013044371A1 (fr) *	2011-09-30	2013-04-04	Switch Materials, Inc.	Dérivés de diarylcyclopentène photochromes et électrochromes comme filtres optiques
US9227986B2 (en)	2011-09-30	2016-01-05	Switch Materials, Inc.	Diarylethene compounds and uses thereof
US10072023B2 (en)	2011-09-30	2018-09-11	Switch Materials, Inc.	Diarylethene compounds and uses thereof
US10556912B2 (en)	2011-09-30	2020-02-11	Switch Materials, Inc.	Diarylethene compounds and uses thereof
US11124524B2 (en)	2011-09-30	2021-09-21	Solutia Canada Inc.	Diarylethene compounds and uses thereof
WO2013106921A1 (fr) *	2012-01-20	2013-07-25	Switch Materials , Inc.	Filtre optique composite

Also Published As

Publication number	Publication date
US20060240197A1 (en)	2006-10-26
AU2003257320A1 (en)	2004-02-25
CA2494920C (fr)	2013-01-22
WO2004015024A1 (fr)	2004-02-19
US7777055B2 (en)	2010-08-17
US20110003966A1 (en)	2011-01-06
US8450503B2 (en)	2013-05-28
JP2005535692A (ja)	2005-11-24
JP4410108B2 (ja)	2010-02-03

Publication	Publication Date	Title
US8450503B2 (en)	2013-05-28	Photochromic and electrochromic compounds and methods of synthesizing and using same
Irie et al.	2014	Photochromism of diarylethene molecules and crystals: memories, switches, and actuators
Fan et al.	2008	Substituent position effect on the properties of isomeric photochromic diarylethenes bearing chlorine atoms
Pu et al.	2010	The effect of substituent position upon unsymmetrical isomeric diarylethenes bearing a methoxy group
Irie	2000	Diarylethenes for memories and switches
Browne et al.	2005	Oxidative electrochemical switching in dithienylcyclopentenes, part 2: effect of substitution and asymmetry on the efficiency and direction of molecular switching and redox stability
Liu et al.	2013	Photochromism of asymmetrical diarylethenes with a pyrrole unit: effects of aromatic stabilization energies of aryl rings
Pu et al.	2005	Syntheses and optoelectronic properties of four photochromic dithienylethenes
Fan et al.	2008	Substituent position effect on the properties of new unsymmetrical isomeric diarylethenes having a chlorine atom
Osuka et al.	2001	Synthesis and photoisomerization of dithienylethene-bridged diporphyrins
Ordronneau et al.	2012	Photochromic metal complexes: Photoregulation of both the nonlinear optical and luminescent properties
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